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The crystal structure of tris(4-methyl-1H-pyrazol-1-yl)methane, C13H16N6

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Zeitschrift für Kristallographie - New Crystal Structures
From the journal Zeitschrift für Kristallographie - New Crystal Structures Volume 237 Issue 2

Abstract

C13H16N6, orthorhombic, Pbca (No. 61), a = 16.097(2) Å, b = 9.8309(13) Å, c = 17.349(2) Å, β = 90°, V = 2745.4(6) Å3, Z = 8, Rgt (F) = 0.0434, wRref(F2) = 0.1302, T = 296(2) K.

CCDC no.: 2142297

The molecular structure is shown in the figure. Table 1 contains crystallographic data and Table 2 contains the list of the atoms including atomic coordinates and displacement parameters.

Table 1:

Data collection and handling.

Crystal: Colourless block
Size 0.20 × 0.10 × 0.10 mm
Wavelength: Mo Kα radiation (0.71073 Å)
μ: 0.08 mm−1
Diffractometer, scan mode: Bruker apex-II, φ and ω
θmax, completeness: 25.5°, >99%
N(hkl)measured, N(hkl)unique, Rint: 19561, 2544, 0.031
Criterion for Iobs, N(hkl)gt: Iobs > 2 σ(Iobs), 1960
N(param)refined: 175
Programs: Bruker [1], Olex2 [2], SHELX [3, 4]
Table 2:

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2).

Atom x y z Uiso*/Ueq
C1 0.21029 (9) 1.08294 (15) 0.55016 (8) 0.0437 (4)
H1 0.187962 1.173265 0.562071 0.052*
C2 0.12640 (10) 0.87939 (17) 0.50670 (9) 0.0504 (4)
H2 0.158921 0.849186 0.465834 0.061*
C3 0.05414 (10) 0.82261 (17) 0.53151 (11) 0.0560 (4)
C4 0.03063 (11) 0.9042 (2) 0.59252 (12) 0.0687 (5)
H4 −0.017326 0.889550 0.621235 0.082*
C5 0.00951 (14) 0.7018 (2) 0.49969 (16) 0.0911 (8)
H5A 0.029605 0.682721 0.448725 0.137*
H5B −0.048988 0.720451 0.497621 0.137*
H5C 0.019226 0.624478 0.532290 0.137*
C6 0.30414 (11) 1.00906 (18) 0.44127 (11) 0.0564 (4)
H6 0.336176 0.943716 0.466151 0.068*
C7 0.30784 (12) 1.0425 (2) 0.36546 (11) 0.0641 (5)
C8 0.24796 (13) 1.1421 (2) 0.35705 (10) 0.0689 (5)
H8 0.236471 1.184603 0.310350 0.083*
C9 0.36499 (18) 0.9829 (3) 0.30556 (16) 0.1057 (9)
H9A 0.415363 1.035060 0.303518 0.159*
H9B 0.338245 0.985171 0.256122 0.159*
H9C 0.377784 0.890467 0.318886 0.159*
C10 0.30912 (10) 1.14057 (17) 0.65582 (9) 0.0478 (4)
H10 0.297547 1.233046 0.659345 0.057*
C11 0.36572 (10) 1.07116 (19) 0.69867 (10) 0.0533 (4)
C12 0.35990 (11) 0.93813 (19) 0.67086 (10) 0.0584 (5)
H12 0.392037 0.866627 0.689368 0.070*
C13 0.41946 (14) 1.1257 (2) 0.76230 (13) 0.0865 (7)
H13A 0.433794 1.218519 0.751420 0.130*
H13B 0.469199 1.072195 0.765949 0.130*
H13C 0.389754 1.121240 0.810215 0.130*
N1 0.14227 (7) 0.98762 (13) 0.55228 (7) 0.0465 (3)
N2 0.08281 (10) 1.00506 (18) 0.60616 (9) 0.0680 (5)
N3 0.24534 (8) 1.08819 (13) 0.47384 (7) 0.0449 (3)
N4 0.20856 (9) 1.17114 (15) 0.42189 (8) 0.0594 (4)
N5 0.27272 (8) 1.05141 (13) 0.60724 (7) 0.0449 (3)
N6 0.30392 (9) 0.92423 (14) 0.61542 (9) 0.0571 (4)

Source of material

Distilled water (30 mL) was added to a 50 mL round bottom flask containing a mixture of 4-methyl-1H-pyrazole(8.2 g, 0.1 mol) and tetra-n-butylammonium bromide (0.32 g, 1 mmol). With vigorous stirring, sodium carbonate (10.5 g, 0.1 mol) was added to the reaction mixture at room temperature. After stirring for 1 h chloroform (30 mL) was added. This mixture was heated at gentle reflux for three days turning to a pale yellow emulsion. The mixture was allowed to cool to room temperature and filtered through a Büchner funnel to remove the excess base. To the filtrate was added diethyl ether (100 mL) and H2O (30 mL). The organic layer was separated and the aqueous layer extracted with diethyl ether (3 × 20 mL). The combined organic layers were washed with brine (20 mL). The organic layer was dried over sodium sulfate and concentrated by rotary evaporation. The resulting pale yellow solid (5.5 g, 65%) was then dried under vacuum. Crystals were obtained by slow evaporation in CH3OH within 10 days.

Comment

Tri(pyrazolyl)methanes are a class of ligands that has attracted much attention in recent years due to their ready coordination to metals in a facial arrangement [5], [6], [7]. These neutral ligands are formally derived from tris(pyrazolyl)borate ligands by replacing the central boron anion with a carbon atom and their generally higher stability than related pyrazolyl boron based systems. Trofimenko reported the syntheses of several tris(pyrazolyl)methane ligands based on pyrazole-3-yl or pyrazole-5-yl substituents and demonstrated that these neutral ligands bind both early (Cr, Mo, W and Mn) and late transition metals pyridine-4-yl substituents (Co, Ni, and Pd). The aim of these changes is to provide a small degree of steric hindrance and considerable coordinative flexibility [8], [9], [10].

Keeping the aforementioned research in mind, we herein describe the synthesis and the crystal structure of a pyrazole-4-yl substituent tri(pyrazolyl)methane. The pyrazole ring (N1, N2, C2–C4) makes dihedral angles of 86.33(11)° and 79.14(10)° with other two pyridine rings (N3, N4, C6–C8 and N5, N6, C10–C12), respectively. In addition, the crystal structure exhibits weak C–H⃛π interactions [C(2)–H(2)⃛Cg2a = 2.99(2) Å; Cg2 is the centroid of pyridine ring (N3, N4, C1–C3); a = 1/2 − x, 1/2 + y, z]. Furthermore, there are a weak π⃛π stacking interactions between pyrazole rings in the crystal structure. The short stacking distance Cg1⃛Cg1b is 3.7954(11) Å, and Cg1 is the centroid of pyrazole ring (N1, N2, C2, C3, C4), a symmetry code for Cg1b was given as (1−x,−y,−z). The stability of crystal structure can be accounted by those interactions.

Corresponding author: Gui-Ling Wu, Department of Chemistry and Chemical Engineering, Qiannan Normal University for Nationalities, Duyun 558000, P. R. China, E-mail:

Funding source: Qiannan Normal University for Nationalities

Award Identifier / Grant number: qnsy2017002

Funding source: Scientific and Technological Project for Agriculture of Qiannan

Award Identifier / Grant number: Qiannankehe[2018]12

  1. Author contributions: All the authors have accepted responsibility for the entire content of this submitted manuscript and approved submission.

  2. Research funding: The authors is grateful to the projects of Qiannan Normal University for Nationalities (qnsy2017002) and the scientific and technological project for agriculture of Qiannan (Qiannankehe[2018]12) for financial support.

  3. Conflict of interest statement: The authors declare no conflicts of interest regarding this article.

References

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Received: 2021-12-07
Accepted: 2022-01-15
Published Online: 2022-01-31
Published in Print: 2022-04-26

© 2022 Gui-Ling Wu, published by De Gruyter, Berlin/Boston

This work is licensed under the Creative Commons Attribution 4.0 International License.

Articles in the same Issue

  1. Frontmatter
  2. New Crystal Structures
  3. Crystal structure of {2,2′-{cyclohexane-1,2-diylbis[(azanylylidene)methylylidene]}bis(2,4-dibromophenolato)-κ4 N,N′,O,O′}copper(II) ─ diethylformamide (1/1), C23H23Br4CuN3O3
  4. The crystal structure of 2-(2-methyl-6-phenyl-4H-pyran-4-ylidene)-1H-indene-1,3(2H)-dione, C21H14O3
  5. Crystal structure of bis((1-methylbenzimidazol-2-yl)methyl)amine, C18H19N5
  6. Crystal structure of (E)-N′-(1-(2-hydroxy-4-methoxyphenyl)ethylidene) isonicotinohydrazide, C15H15N3O3
  7. Crystal structure of 2-((4-phenyl-5-(pyridin-4-yl)-4H-1,2,4-triazol-3-yl)thio)acetonitrile, C15H11N5S
  8. The crystal structure of 2,2′-((1E,1′E)-hydrazine-1,2-diylidenebis(methaneylylidene))bis(4-chlorophenol), C14H10Cl2N2O2
  9. Dichlorido-{2,6-bis(4,5-dihydro-1H-pyrazol-3-yl)pyridine-κ3 N,N′,N″}zinc(II), C11H9C12N5Zn
  10. The crystal structure of dichlorido-(2-((4-phenyl-2H-1,2,3-triazol-2-yl)methyl)pyridine-κ2N,N′)palladium(II), C14H12Cl2N4Pd
  11. The crystal structure of 1-(N1-benzyl-2-methyl-4-nitro-imidazol-5-yl)-4-(prop-2-yn-1-yl) piperazine, C18H21N5O2
  12. Crystal structure of (μ4-(1,2,4,5-tetra(1,2,4-triazol-1-ylmethyl)-benzene-κ4N:N1:N2:N3)disilver(I) diperchlorate
  13. The crystal structure of 1-(2-bromoethane)-4-amine-3,5-dinitropyrazole, C5H6Br1N5O4
  14. Crystal structure of (E)-1-(4-benzyl-3,5-dioxomorpholin-2-ylidene)ethyl acetate, C15H15N1O5
  15. The crystal structure of poly[diaqua-(μ2-1,2,4,5-tetrakis(1,2,4-triazol-1-ylmethyl)-benzene-κ2N:N′)-bis(μ3-terephthalato-κ3O:O′:O′′)dicadmium(II)], C17H15N6O5Cd
  16. Crystal structure of (E)-N′-(1-(5-chloro-2-hydroxyphenyl) ethylidene)thiophene-2-carbohydrazide, C13H11ClN2O2S
  17. The crystal structure of [(2,2′-bipyridine-k2 N,N)-bis(6-phenylpyridine-2-carboxylato-k2 N,O)cobalt(II)]-monohydrate, C36H26N4O5Co
  18. Crystal structure of (E)-N′-(2-chloro-6-hydroxybenzylidene)-3-hydroxybenzo-hydrazide monohydrate, C14H13ClN2O4
  19. Crystal structure of 1,1′-(methylene)bis(pyridin-1-ium) bis(1,2-dicyanoethene-1,2-dithiolato-κ2S:S)nickel(II), C42H30N14Ni2S8
  20. Crystal structure of 1,1′-(1,2-ethanediyl)bis(pyridin-1-ium) bis(1,2-dicyanoethene-1,2-dithiolato-κ2 S:S)nickel(II), C20H14N6NiS4
  21. The crystal structure of 1-methyl-1H-pyrazol-2-ium nitrate, C4H7O3N3
  22. The crystal structure of 4,4′-diselanediylbis(8-(hexyloxy)-3,6-dimethyl-1-(piperidin-1-yl)isoquinoline-7-carbonitrile), C46H60N6O2Se2
  23. The crystal structure of tris(6-methylpyridin-2-yl)phosphine selenide, C18H18N3PSe
  24. The crystal structure of 1,2-bis(2,4-dinitro-1H-imidazol-1-yl)ethane ─ acetone (1/1), C11H12N8O9
  25. Crystal structure of [diaqua[2,2′-(1,2-phenylene)bis(1H-imidazole-4-carboxylato-5-carboxy)-κ4N,N′,O,O′]nickel(II)] tetrahydrate, C16H12N4NiO10·4H2O
  26. The crystal structure of tris(4-methyl-1H-pyrazol-1-yl)methane, C13H16N6
  27. The crystal structure of 5,6-dichloro-2-(quinolin-8-yl)isoindoline-1,3-dione, C17H8Cl2N2O2
  28. Crystal structure of (E)-(2-methoxy-benzylidene)-(4-[1,2,4]triazol-1-yl-phenyl)-amine, C16H14N4O
  29. The crystal structure of (Z)-2-(4-(4-bromophenyl)thiazol-2-yl)-4-(3-hydroxybut-2-enoyl)-5-methyl -1,2-dihydro-3H-pyrazol-3-one – methanol (1/1), C18H18N3O4S
  30. Crystal structure of tetraaqua-tris(nitrato-κ2 O,O′) erbium(III) monohydrate, Er(NO3)3·5H2O, H10ErN3O14
  31. The crystal structure of 1-methyl-2-nitro-1H-imidazole 3-oxide, C4H5N3O3
  32. The crystal structure of 1-methyl-2-nitroimidazole, C4H5N3O2
  33. The crystal structure of 2-carboxyl-4-nitroimidazole monohydrate, C4H5N3O5
  34. Crystal structure of bis[hydrido-hexaphenylcarbodiphosphoran][tetra-trifluoromethyl-(μ-diiodo)-diplatinat]
  35. The crystal structure of poly[μ2-aqua- aqua-(μ3-(E)-2-(4-((2-carbamothioylhydrazineylidene)methyl)phenoxy)acetato-κ3 O:S:S)sodium(I)], C10H14N3O5SNa
  36. The twinned crystal structure of [4,4′-bipyridine]-1,1′-diium hexachloridostannate(IV), C10H10N2SnCl6
  37. The crystal structure of [(2,2′-bipyridine-k2 N,N)-bis(6-phenylpyridine-2-carboxylate-k2 N,O)copper(II)], C34H24N4O4Cu
  38. Crystal structure of trans-1,2-bis(pyridinium-4-yl) ethylene bis(2-carboxy-4-bromobenzoate) – water (1/4), C14H14BrNO6
  39. Crystal structure of poly[diaqua-(μ3-fumarato)-(μ3-maleato)-(μ4-1,2,4,5-tetrakis((1H-1,2,4-triazol-1-yl)methyl)benzene)tetracadmium(II)] dihydrate, C34H32N12O9Cd4
  40. Crystal structure of a second modification of Pachypodol, C18H16O7
  41. Crystal structure of methyl 2-(4-(2-(cyclopentyl-amino)-1-(N-(4-methoxyphenyl)-1-methyl-5-phenyl-1-H-pyrazole-3-carboxamido)-2-oxoethyl)phenyl)acetate, C34H36N4O5
  42. The crystal structure of catena-poly[(m2-4,4′-bipyridine-κ2 N:N)-bis(6-phenylpyridine-2-carboxylato-κ2 N,O) zinc(II)], C34H24N4O4Zn
  43. The crystal structure of hexaquamagnesium(II) (2,4-bis(nitroimino)-6-oxo-1,3,5-triazinane-1,3-diide), C3H15MgN7O12
  44. The crystal structure of 7-Bromo-2-(4-chloro-phenyl)-quinoxaline, C14H9BrClN2
  45. Crystal structure of methyl 4-{[4-(4-cyanobenzamido)phenyl]amino}benzofuro[2,3-d]pyrimidine-6-carboxylate, C26H17N5O4
  46. The crystal structure of (4SR)-7-(3,4-dichlorobenzyl)-4,8,8-trimethyl-7,8-dihydroimidazo[5,1c][1,2,4]triazine-3,6(2H,4H)-dione, C15H16Cl2N4O2
  47. Crystal structure of catena-poly[{μ2-3-carboxy-2,3-bis((4-methylbenzoyl)oxy)propanoato-κ2 O:O′}tris(methanol-κ1 O)lanthanum(III)], C63H63LaO27
https://doi.org/10.1515/ncrs-2021-0467
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Articles in the same Issue

  1. Frontmatter
  2. New Crystal Structures
  3. Crystal structure of {2,2′-{cyclohexane-1,2-diylbis[(azanylylidene)methylylidene]}bis(2,4-dibromophenolato)-κ4 N,N′,O,O′}copper(II) ─ diethylformamide (1/1), C23H23Br4CuN3O3
  4. The crystal structure of 2-(2-methyl-6-phenyl-4H-pyran-4-ylidene)-1H-indene-1,3(2H)-dione, C21H14O3
  5. Crystal structure of bis((1-methylbenzimidazol-2-yl)methyl)amine, C18H19N5
  6. Crystal structure of (E)-N′-(1-(2-hydroxy-4-methoxyphenyl)ethylidene) isonicotinohydrazide, C15H15N3O3
  7. Crystal structure of 2-((4-phenyl-5-(pyridin-4-yl)-4H-1,2,4-triazol-3-yl)thio)acetonitrile, C15H11N5S
  8. The crystal structure of 2,2′-((1E,1′E)-hydrazine-1,2-diylidenebis(methaneylylidene))bis(4-chlorophenol), C14H10Cl2N2O2
  9. Dichlorido-{2,6-bis(4,5-dihydro-1H-pyrazol-3-yl)pyridine-κ3 N,N′,N″}zinc(II), C11H9C12N5Zn
  10. The crystal structure of dichlorido-(2-((4-phenyl-2H-1,2,3-triazol-2-yl)methyl)pyridine-κ2N,N′)palladium(II), C14H12Cl2N4Pd
  11. The crystal structure of 1-(N1-benzyl-2-methyl-4-nitro-imidazol-5-yl)-4-(prop-2-yn-1-yl) piperazine, C18H21N5O2
  12. Crystal structure of (μ4-(1,2,4,5-tetra(1,2,4-triazol-1-ylmethyl)-benzene-κ4N:N1:N2:N3)disilver(I) diperchlorate
  13. The crystal structure of 1-(2-bromoethane)-4-amine-3,5-dinitropyrazole, C5H6Br1N5O4
  14. Crystal structure of (E)-1-(4-benzyl-3,5-dioxomorpholin-2-ylidene)ethyl acetate, C15H15N1O5
  15. The crystal structure of poly[diaqua-(μ2-1,2,4,5-tetrakis(1,2,4-triazol-1-ylmethyl)-benzene-κ2N:N′)-bis(μ3-terephthalato-κ3O:O′:O′′)dicadmium(II)], C17H15N6O5Cd
  16. Crystal structure of (E)-N′-(1-(5-chloro-2-hydroxyphenyl) ethylidene)thiophene-2-carbohydrazide, C13H11ClN2O2S
  17. The crystal structure of [(2,2′-bipyridine-k2 N,N)-bis(6-phenylpyridine-2-carboxylato-k2 N,O)cobalt(II)]-monohydrate, C36H26N4O5Co
  18. Crystal structure of (E)-N′-(2-chloro-6-hydroxybenzylidene)-3-hydroxybenzo-hydrazide monohydrate, C14H13ClN2O4
  19. Crystal structure of 1,1′-(methylene)bis(pyridin-1-ium) bis(1,2-dicyanoethene-1,2-dithiolato-κ2S:S)nickel(II), C42H30N14Ni2S8
  20. Crystal structure of 1,1′-(1,2-ethanediyl)bis(pyridin-1-ium) bis(1,2-dicyanoethene-1,2-dithiolato-κ2 S:S)nickel(II), C20H14N6NiS4
  21. The crystal structure of 1-methyl-1H-pyrazol-2-ium nitrate, C4H7O3N3
  22. The crystal structure of 4,4′-diselanediylbis(8-(hexyloxy)-3,6-dimethyl-1-(piperidin-1-yl)isoquinoline-7-carbonitrile), C46H60N6O2Se2
  23. The crystal structure of tris(6-methylpyridin-2-yl)phosphine selenide, C18H18N3PSe
  24. The crystal structure of 1,2-bis(2,4-dinitro-1H-imidazol-1-yl)ethane ─ acetone (1/1), C11H12N8O9
  25. Crystal structure of [diaqua[2,2′-(1,2-phenylene)bis(1H-imidazole-4-carboxylato-5-carboxy)-κ4N,N′,O,O′]nickel(II)] tetrahydrate, C16H12N4NiO10·4H2O
  26. The crystal structure of tris(4-methyl-1H-pyrazol-1-yl)methane, C13H16N6
  27. The crystal structure of 5,6-dichloro-2-(quinolin-8-yl)isoindoline-1,3-dione, C17H8Cl2N2O2
  28. Crystal structure of (E)-(2-methoxy-benzylidene)-(4-[1,2,4]triazol-1-yl-phenyl)-amine, C16H14N4O
  29. The crystal structure of (Z)-2-(4-(4-bromophenyl)thiazol-2-yl)-4-(3-hydroxybut-2-enoyl)-5-methyl -1,2-dihydro-3H-pyrazol-3-one – methanol (1/1), C18H18N3O4S
  30. Crystal structure of tetraaqua-tris(nitrato-κ2 O,O′) erbium(III) monohydrate, Er(NO3)3·5H2O, H10ErN3O14
  31. The crystal structure of 1-methyl-2-nitro-1H-imidazole 3-oxide, C4H5N3O3
  32. The crystal structure of 1-methyl-2-nitroimidazole, C4H5N3O2
  33. The crystal structure of 2-carboxyl-4-nitroimidazole monohydrate, C4H5N3O5
  34. Crystal structure of bis[hydrido-hexaphenylcarbodiphosphoran][tetra-trifluoromethyl-(μ-diiodo)-diplatinat]
  35. The crystal structure of poly[μ2-aqua- aqua-(μ3-(E)-2-(4-((2-carbamothioylhydrazineylidene)methyl)phenoxy)acetato-κ3 O:S:S)sodium(I)], C10H14N3O5SNa
  36. The twinned crystal structure of [4,4′-bipyridine]-1,1′-diium hexachloridostannate(IV), C10H10N2SnCl6
  37. The crystal structure of [(2,2′-bipyridine-k2 N,N)-bis(6-phenylpyridine-2-carboxylate-k2 N,O)copper(II)], C34H24N4O4Cu
  38. Crystal structure of trans-1,2-bis(pyridinium-4-yl) ethylene bis(2-carboxy-4-bromobenzoate) – water (1/4), C14H14BrNO6
  39. Crystal structure of poly[diaqua-(μ3-fumarato)-(μ3-maleato)-(μ4-1,2,4,5-tetrakis((1H-1,2,4-triazol-1-yl)methyl)benzene)tetracadmium(II)] dihydrate, C34H32N12O9Cd4
  40. Crystal structure of a second modification of Pachypodol, C18H16O7
  41. Crystal structure of methyl 2-(4-(2-(cyclopentyl-amino)-1-(N-(4-methoxyphenyl)-1-methyl-5-phenyl-1-H-pyrazole-3-carboxamido)-2-oxoethyl)phenyl)acetate, C34H36N4O5
  42. The crystal structure of catena-poly[(m2-4,4′-bipyridine-κ2 N:N)-bis(6-phenylpyridine-2-carboxylato-κ2 N,O) zinc(II)], C34H24N4O4Zn
  43. The crystal structure of hexaquamagnesium(II) (2,4-bis(nitroimino)-6-oxo-1,3,5-triazinane-1,3-diide), C3H15MgN7O12
  44. The crystal structure of 7-Bromo-2-(4-chloro-phenyl)-quinoxaline, C14H9BrClN2
  45. Crystal structure of methyl 4-{[4-(4-cyanobenzamido)phenyl]amino}benzofuro[2,3-d]pyrimidine-6-carboxylate, C26H17N5O4
  46. The crystal structure of (4SR)-7-(3,4-dichlorobenzyl)-4,8,8-trimethyl-7,8-dihydroimidazo[5,1c][1,2,4]triazine-3,6(2H,4H)-dione, C15H16Cl2N4O2
  47. Crystal structure of catena-poly[{μ2-3-carboxy-2,3-bis((4-methylbenzoyl)oxy)propanoato-κ2 O:O′}tris(methanol-κ1 O)lanthanum(III)], C63H63LaO27
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